Details
| Original language | English |
|---|---|
| Qualification | Doctor rerum naturalium |
| Awarding Institution | |
| Supervised by |
|
| Date of Award | 23 Feb 2023 |
| Place of Publication | Hannover |
| Publication status | Published - 2023 |
Abstract
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Hannover, 2023. 571 p.
Research output: Thesis › Doctoral thesis
}
TY - BOOK
T1 - Synthesis of natural and non-natural terpenoid natural products
AU - Moeller, Malte
N1 - Doctoral thesis
PY - 2023
Y1 - 2023
N2 - Terpenes represent the largest and most structurally diverse group of natural products. Sesquiterpenes are well known by their distinctive smells and tastes and are used extensively in the perfume and food industries. These are comprised of repeating isoprene units that are constructed by condensation of the biosynthetic building blocks isopentenyl- and dimethylallyl pyrophosphate. The simple linear precursors are then transformed by terpene cyclases to diverse polycyclic products. In these cascade reactions the precursors undergo multiple changes in bonding, hybridization and stereochemistry. This complex cascade is unique for each cyclase leading to a huge variety of different possible struc-tures. In this thesis, a from biotransformation experiments with unnatural FPP-derivatives utilizing STC Bot2 isolated tricyclus was waimed to be synthesized to verify its stereochemistry and explore further properties via derivatization. On the other hand, farnesyl derivatives that bear oxidations at the ter-minal methyl groups were synthesized. By this, oxidations at positions which would usually be later on oxidized by follow up enzymatic reactions are included. These substrates were synthesized using different kinds of chemistry around double and triple bonds to ensure the necessary regioselectivity. New products from biotransformation assays were isolated and their structures were elucidated.
AB - Terpenes represent the largest and most structurally diverse group of natural products. Sesquiterpenes are well known by their distinctive smells and tastes and are used extensively in the perfume and food industries. These are comprised of repeating isoprene units that are constructed by condensation of the biosynthetic building blocks isopentenyl- and dimethylallyl pyrophosphate. The simple linear precursors are then transformed by terpene cyclases to diverse polycyclic products. In these cascade reactions the precursors undergo multiple changes in bonding, hybridization and stereochemistry. This complex cascade is unique for each cyclase leading to a huge variety of different possible struc-tures. In this thesis, a from biotransformation experiments with unnatural FPP-derivatives utilizing STC Bot2 isolated tricyclus was waimed to be synthesized to verify its stereochemistry and explore further properties via derivatization. On the other hand, farnesyl derivatives that bear oxidations at the ter-minal methyl groups were synthesized. By this, oxidations at positions which would usually be later on oxidized by follow up enzymatic reactions are included. These substrates were synthesized using different kinds of chemistry around double and triple bonds to ensure the necessary regioselectivity. New products from biotransformation assays were isolated and their structures were elucidated.
U2 - 10.15488/13292
DO - 10.15488/13292
M3 - Doctoral thesis
CY - Hannover
ER -